Are You Kidding Me?
by LivingTheSPNLife
Summary: When Jess needs back-up on a hunt in Stars Hollow, Bobby is usually his go-to guy. But when Bobby isn't up to hunting, he sends in Sam and Dean, two hunters that Jess has never met. What will happen when they meet?
1. Chapter 1

**A/N: This is** **set to season 3 of Gilmore Girls and season 2 of Supernatural. I know Rufus wasn't introduced to the Supernatural fandom until season 3, but I needed something to use for Bobby's voicemail that sounded like him.**

**Disclaimer: I** **do not own Supernatural or Gilmore Girls. I wish I did, but sadly I don't.  
**

_Ring_, _ring_! _Ring_, _ring_! _Ring_, _ring_!

_Click_!

"You've reached Bobby Singer. If this is you calling again, Rufus, go die in a hole," the voicemail machine answered.

"Damn it, Bobby, answer the freaking phone!" a young male voice exclaimed, hanging up furiously.

_Ring_, _ring_! _Ring_, _ring_!

Bobby Singer sat up in bed and rubbed the three hours of sleep from his eyes as he snatched up his phone from the dresser next to the bed. He had hoped that the caller would leave a simple message asking Bobby to get back to him in the morning. After ten calls, Bobby knew that wouldn't happen.

"Hello?" Bobby asked in a grumpy tone.

"Finally!" the caller exclaimed in frustration. "Bobby, it's Jess. I'm working a job here in Stars Hollow and I think that whatever it is that I'm hunting is going to be a two person job."

"Boy, do you know what time it is?"

"Yeah, it's about three a.m."

"And you didn't think that this could wait a few more hours?"

"People are dying, Bobby, I thought that this was a little more important than sleep," Jess said with a frustrated growl.

In a low, angry tone, Bobby replied, "Boy, mind your tone with me. I just got back from a job four hours ago, so I apologize for wanting to get some rest before I have to deal with idjits all day."

"Bobby -"

"Save it, Jess. I'll call you some back-up, but do me a favor and don't call me in the middle of the night unless you decide to change your attitude."

Bobby clicked off the phone and muttered, "Idjit." He grabbed his cell phone and scrolled down until he found the number of the two hunters he knew would be capable of helping Jess. Bobby hit the call button and listened to the phone ring five times before somebody picked up.

"This better be good, Bobby," an irritated voice answered.

"I found you boys a job. Stars Hollow, Connecticut. Don't know what's out there to hunt, but I have the number of the hunter who needs help," Bobby said, rubbing his tired eyes.

Silence answered Bobby.

"You still on the line, Dean?"

There was some shuffling on the other line and another voice answered, "Hey, Bobby, it's Sam. Dean's… well, you know Dean when he hasn't gotten his four hours. He did mumble something about a job you had for us?"

"You got a pen and paper?"

"Right here."

Bobby relayed the information he had given a sleepy Dean. There was a brief pause once Bobby gave Sam Jess's number.

"Thanks, Bobby," Sam said before he clicked off the phone, leaving Bobby to rest.

~~~~~~~~~

Sam tossed Dean's cell phone on the dresser and turned toward the sleeping figure on the bed next to his. Sam placed his hand on the middle of his older brother's back and shook him, saying, "Dean, you have to get up."

Dean grunted in reply and moved his pillow to the top of his head to cover his ears so that he wouldn't be able to hear Sam.

Sam sighed. "Before you get pissed off, just remember that you asked for this."

Sam removed his hand from Dean's back and jumped on it, causing his brother to hiss in pain. Sam wiggled around, mushing Dean and making himself comfortable.

"Get your Sasquatch form off me," Dean mumbled under the pillow.

"Not until you promise to get up. I'll just keep hopping on and off until you do."

"Damn it, Sam!"

"Or maybe I'll take the Impala out for a drive."

Dean groaned. "Fine. Fine!"

Sam hopped off Dean and smiled. "You pack; give yourself some exercise before we hit the road. I'll go start the car."

Dean lifted his head from underneath the pillow. "You know you're not driving, right?"

Sam chuckled and shook his head. "Yeah, I kinda figured that. We still need to do some research, and you don't seem like you're in the researching mood, so yeah."

Dean thought the comment over and nodded in agreement. He never was in a research mood – that was all Sam, but as to why his younger brother enjoyed it, Dean didn't have a clue.

~~~~~~~~~~~

"So, what's the news on this Stars Hollow gig Bobby gave us?" Dean asked Sam, lowering the radio.

The boys were cruising down the highway in the Impala, Sam on his laptop doing research and Dean driving as he sang along to the radio.

Sam glanced up from his laptop. "Well, for it being a small town, Stars Hollow sure has a lot of obits in its papers lately."

"How did they die?"

"According to the paper, most of them died in their sleep."

Dean's eyes flickered over to Sam. "So, what, Freddy Krueger's visiting the town and killing everyone?"

"I don't know, maybe the hunter we're supposed to meet will have more Intel." Sam closed his laptop and set it on the backseat. "How much longer until we get there, anyway?"

"Like two hours, I think."

Sam nodded. "I'll call Jess once we hit Hartford."

"Why don't you call him now?"

Sam laughed. "Dean, it's five in the morning and we're two hours away; don't you think it's a bit early to be calling?"

"Bastard woke us up at three a.m.; it'd just be returning the favor."

Sam sighed and shook his head, wondering why he even bothered to ask the question.

"Since we have two more hours of desolate road ahead of us," Dean said, placing his hand over the radio volume, "I say we listen to some tunes."

Dean raised the volume of the stereo and Hot Blooded blasted through the car.

_This oughtta be fun,_ Sam thought as Dean began to sing, off-key, "I'm hot blooded! Check it and see!"


	2. Chapter 2: A Drop In The Ocean

**A/N: Thank you all for reading this! I did not think I would get a lot of reads. If you have any constructive criticism or good feedback, don't be afraid to share it! **

Jess Mariano was asleep on his blow-up mattress in his Uncle Luke's small apartment above Luke's Diner. The mattress was quite comfy with one of Luke's plaid comforters over it, to Jess's surprise. When Jess had first laid eyes upon the mattress's crumpled up form stuffed in Luke's tiny linen closet, he had thought that he wouldn't ever have a good night's rest, but his opinion of things had recently begun to change.

When Jess first arrived at Star's Hollow, he hated everything about the town. He had hated the way the town looked with its charming structures and old town feel, he'd hated the way the town smelt on occasion because of rotten eggs Kirk had forgotten about from last Easter or because a pickle truck flipped and left its pickles everywhere, he'd hated the festivals the town threw on for no reason, and, most importantly, Jess had hated the people, every single one with their smiles and their "you're going to love it here".

That all changed the moment he saw Rory. She made everything he'd hated not so bad anymore. She was smart, funny, and, for some unknown reason, she had been nice to Jess. At first, their relationship was rocky, what with Rory having a boyfriend who hated Jess and her placing him in the friend zone. But Jess was determined, and who would've seen that coming? There was something about Rory that made her unlike the other girls Jess had dated, and he had been willing to do anything to get her back.

Now that she was his girlfriend, Jess had to find time in his busy schedule to see her, work at Luke's, work at Wal-Mart, go to school to get a useless education, and hunt on occasion – if the problem wasn't too far away. Jess's current hunt was in Stars Hollow, the town he thought would be the last place anything supernatural would visit – or want to visit.

People around the town – old and young - were dropping like flies. Jess originally hadn't thought much of it because the deaths had come in their sleep, but as more people began dying, Jess knew something was up. He'd started his investigation two days ago, eavesdropping on what the townsfolk had been saying about each person. People had been mentioning a change in each person's behavior before they died. The deceased had seemed more tired and irritable during the days leading to their deaths. The next day, Jess went to the library and scoured through countless websites, searching for some creature that preyed on humans while they slept.

Jess found a few profiles that fit the bill, so he went to check out the lake just outside of town since most of the creatures seemed like they would dwell there. He waited a few hours after Luke fell asleep to sneak out of the apartment, hop into his car, and drive away.

Jess parked his car and walked to the bridge, searching for a sign of life. Jess had spent minutes looking around the bridge when he heard a splash from the water below him. He peered down at the lake, but everything looked the same. However, Jess noted the scent of fish from behind him, so he turned and found himself staring at a six-foot tall creature that had an octopus head and long tentacles.

Jess drew out his silver knife, hoping that it would do against the creature. Living with Luke, Jess had no place to store weapons other than the knife his father had given him when he was a little boy. Jess held up his knife as one of the creature's tentacles swung at him. Jess slashed the knife around and connected with the tentacle, causing the creature to hiss in pain as a piece of the tentacle plopped on the ground. The creature glared at Jess with angry, red eyes and swung its seven uninjured tentacles at the hunter. Two tentacles slapped Jess's face while the other five struck his body hard as hammers. The force of the attack knocked Jess into the water.

The creature jumped into the river and wrapped Jess in its tentacles, squeezing the life out of him. Jess still gripped his knife tight in his hands and brought it to one of the tentacles holding him, slicing through it as if it were a piece of rope. The creature squealed in pain and lessened its hold on Jess. Jess struggled out of the tentacles, hacking away at the creature as he fought his way above water for air. Jess felt as though he were about to pass out when he cut is way through the tentacles restraining him. He quickly swam ashore and sucked in the cool fresh air.

Jess pulled himself out of the water and ran to his car. Only when he was driving back to Luke's did Jess take nice, deep breaths of air. Jess knew he was in over his head, so he called Bobby for back-up. Jess wasn't sure when to expect the help Bobby promised, so he drove back to Luke's and snuck back in unnoticed. He flopped onto his blow-up mattress and fell asleep for a few hours until he heard his phone buzzing.

Jess opened his eyes and snatched up his phone, glancing around the apartment for Luke. Luke's bed was tucked in nicely, and none of the lights were one, so Jess figured he was already downstairs opening the diner. The clanking of pots and pans confirmed that. Jess looked back at the unknown answer calling his phone.

"Hello?" Jess answered, stifling a yawn.

"Is this Jess Mariano?" a familiar male voice asked.

Jess creased his eyebrows, trying to connect the voice to a face. "Yeah. Who are you?"

"My name is Sam. Bobby Singer sent my brother and me to help you with a hunt."

Had Jess met a hunter named Sam before? He didn't think he had, and Sam didn't seem to know Jess, so maybe Sam's voice just reminded him of someone….

"So are you guys here yet?" Jess asked, shaking off his thoughts.

"We're in Hartford; we weren't sure how to find you in Stars Hollow, so I thought I would call ahead to see if there's a place we could meet?"

Jess tilted his face in thought. "There's a dance studio in the middle of the town that shouldn't be used for a few more hours. Meet me there in thirty."

With that, Jess hung up the phone.


	3. Chapter 3: You're Not Sam, You're Dean!

**A/N: Thank you all for the great reviews! Sorry the updates have been slow, I've been busy. But I will update at least once a week, if not more. I'm glad you all have enjoyed the story! You rock, love you all!**

"Nice talking to you, too," Sam said sarcastically as he hit the _end call_ button on his phone.

Dean glanced at Sam in the corner of his eye. "So, what'd he say?"

Sam grabbed his laptop and turned it on. "Jess said to meet him at a dance studio in thirty. So, now I have to go online to find a map of Stars Hollow to see if I can find the damn thing."

"Jess didn't say where it was?"

"Nope. He hung up the phone as soon as he could; guess he's not one for talking."

Dean shrugged. "Don't know, don't really care."

Thirty minutes later, the boys rolled into town and found Ms. Patty's Dance Studio. Dean parked the boys' shiny black, 1967 Impala on the side of the road and got out of the car.

"This is the place?" Dean asked Sam as he slammed shut his car door.

Sam nodded, walking up to the entrance. He slid open the door and the two brothers slipped inside. The interior of the studio contained a podium, rows and rows of chairs, and a boy with black, curly hair sitting in the last row with a sour look on his face.

When Jess saw Sam and Dean walk in, his face wrinkled with anger. "You've got to be kidding me," Jess said, standing up.

Sam and Dean looked at each other with confused looks. "Excuse me?" Sam said.

Jess glared at Sam. "Very funny, Dean. Decide to play hunter with your friend Ken Doll to get back at me for dating Rory?"

"What are you talking about?"

"I think somebody had one too many drinks before they came here," Dean whispered to Sam.

"I'm out of here," Jess said, turning away from the boys and walking toward the nearest exit.

"Great, Bobby sent us to help a drama king," Dean said with a roll of his eyes. "If you walk out that door, Jess, know that we're not coming back and Bobby won't send you any more help. You'll have to hunt this thing on your own."

Jess paused, turning toward the brothers. "You want me to work with you two posers?"

"What the hell is your problem?" Sam asked, sick of Jess's attitude.

Jess pointed at Sam. "You. You're my problem. You really expect me to believe you're a hunter, Dean?"

Dean raised a hand and pointed to himself. "I'm Dean." He pointed to Sam. "That's my brother Sam."

Jess shook his head. "Nice try, but I think I know what Dean looks like enough to recognize that 'Sam' is him."

"Do you need to see my birth certificate or something? Establishing that my name's Sam shouldn't be this hard," Sam said with a frustrated sigh. "Hell, you could Google me."

"Find me a laptop and I will."

"Dean, do you mind grabbing my laptop from the backseat?"

"No problem," Dean said.

Dean walked out to the car and grabbed out Sam's laptop. When he walked back inside, Sam and Jess were watching each other. Dean handed Sam his laptop so that he could look himself up. A minute later and Sam walked up to Jess, showing the boy proof that he was Sam Winchester, and not Dean.

"If you aren't Dean, then why do you look like a carbon copy of him?" Jess asked, crossing his arms.

Sam and Dean exchanged looks. "We don't look too much alike," Dean said. "I'm the handsomer one." Sam rolled his eyes.

"Not your brother Dean. The Dean that lives here. The one I mistook you for."

Sam shrugged. "I don't know."

Jess nodded. "One more thing." He looked at Dean with a questioning brow. "I read online that you died and were a murderer."

Dean chuckled. "Yeah, that's what happens when you run into a homicidal shape shifter."

"Well, I guess now that we've established who you both are, we should talk about the job I've been working."

"You figure out what's been causing the Freddy Krueger killings?" Dean asked.

Jess nodded, looking up something on Sam's laptop. "Yeah, I think I figured out what we're up against. I had a run-in with it earlier this morning. Here we go." Jess flipped the laptop so that Sam and Dean could see it.

"An Illithid? What the hell is that?" Dean asked.

"A creature that dwells in the water and feeds off people's nightmares and looks like some weird thing with an octopus head," Jess answered. "I didn't know what it was, but I figured I'd check out the lake at the edge of town and it attacked me with its stupid tentacles."

"You got tentacled?" Dean asked, trying not laugh as an image of Jess getting bitch slapped by a tentacle entered his mind.

Jess glared at Dean. "Can we just focus on stopping it before somebody else drops dead?"

"How do we kill it?" Sam asked, getting everyone back on track.

"Doesn't say. Far as anyone knows they're just in some video game."

"So we don't know how to kill it. Awesome. Makes our job that much harder," Dean said with a roll of his eyes.

"I attacked it with a silver knife and cut off a tentacle earlier. So blades work," Jess said, recalling the creature's creepy, large tentacles. He could almost feel them touching him again.

"Would guns work, maybe?" Dean asked Sam.

Sam tilted his head in thought. "It's a possibility. I'd rather shoot it than get up close and personal."

Dean nodded. "So it's settled, then. I say we leave now and kill this son of a bitch before noon."

"One problem with that," Jess said. "It's daylight hours, there's going to be plenty of people passing by the bridge throughout the day. People, cars, delivery trucks; there's no way we'll through before sun down."

"Then Sam and I'll pose as FBI and say we need to shut down the bridge for a murder investigation or something." Jess shook his head.

"You're forgetting that Sam here looks like some kid in town. Taylor would never buy that."

Dean let out a frustrated growl. "Then what the hell are we supposed to do? The longer we wait, the better chance that thing has of grabbing another snack."

"Would it be possible for you to talk to this Taylor guy?" Sam asked Jess.

Jess chuckled and shook his head. "Yeah, Taylor kind of hates me. He wouldn't believe me. But…." Jess trailed off, looking at Sam. "He likes Dean, so maybe you pose as him. Talk to Taylor, say you know a guy that could patch up the bridge."

Sam laughed and said, "No, no, no. What if people started talking to me, thinking I was him? I don't even know how he acts, or if we even look that much alike."

"You do. You're like his freakin' doppelganger. I could tell you all of that, give you some background information." Jess at least hoped he would be able to offer that. Truthfully, he didn't know Dean that well, aside from what he saw when Dean had been dating Rory.

Sam sighed, seeing no other option than waiting until nightfall. "You really think we could pull this off?"

"Of course," Jess said, his tone not sounding too sure.

Sam glanced down at Jess and said, "Fine. Let's start this lesson." Sam hoped they really could pull this off. Jess didn't seem too sure of himself, and Sam wasn't sure if it was because Jess was worried about giving Sam good information, Sam's acting, or both.

Suddenly there was a knock on the door and a female voice said, "Is anyone in there? I thought I heard voices!"


	4. Chapter 4: It's Time For A Test!

**A/N: I know I should've updated sooner, but I've been busy and letting my laziness get the best of me! I promise to tell it to go away next time and I'll update sooner. Thank you all again for reading! I would love to hear any comments and/or constructive criticisms you may have! You guys rock!  
- LivingTheSPNLife  
**

Sam and Dean looked at Jess with wide eyes. Jess pointed to a door across the room and motioned for them to go through it. Sam and Dean did as instructed and quickly exited the dance studio. Jess followed them out, quietly closing the door. He looked around to make sure the coast was clear and ran across the street.

"Where are we going?" Sam asked, jogging to catch up with Jess.

"Some place away from Miss Patty. If she sees you, she'd talk to you, thinking you were Dean." Jess stopped running once they reached an area secluded by trees. "Okay, I don't think anyone will see us, not yet at least. So, let's start your lesson. I guess background information would be good to know. Your name is Dean Forrester, you are 18, you live with your parents – whose names I don't know – and your younger sister named Clara. You play hockey and go to Stars Hollow High. You're dating some chick named Lindsey and you used to date my girlfriend Rory. Her mother's name is Lorelai, in case you run into her. Oh, and we hate each other."

Sam nodded, absorbing all of the information. "How am I supposed to know who's who?"

Jess thought about that for a moment. "I don't know. We'll just see how that goes."

"Awesome," Sam muttered. "Okay, well if I run into people, how do I act?"

"You're generally friendly to people, not to me, of course, but to everyone else. And there's Kirk, we all get frustrated with him sometimes. Trust me; you'll know who he is once you speak to him. Oh, and you and Rory have started to be friends, which I don't like, but I put up with for her. So if someone waves to you or says hi, you can wave or say hi back. Also, you walk around like you're not that confident. Your eyes don't look up to high, your shoulders are slumped, your hands are in your pockets, and back is hunched over a bit."

"Like this?" Sam imitated what Jess had said.

"Perfect. I think you're ready. We should test you."

Sam's face dropped. "No, no, no, I just want to talk to that Taylor guy and be done with it."

Jess shook his head. "We have to make sure you know what you're doing. It shouldn't be too bad." _I hope._

Dean chuckled and patted Sam on the back. "Come on, Sammy, if you embarrass yourself it's not like you're the one who lives here," he said. "See? There's plenty of people." Dean pointed to the street bustling with people getting ready for work.

Jess looked over to the people, seeing some prospects. He nodded in approval and turned to Sam, handing him a book from his back pocket.

"The hell is this for?" Sam asked; his face wrinkled in confusion.

"You are going to sit down at the park bench a few feet away from these bushed and read that book while your brother and I will listen to your conversations from here, because, trust me, people _will_ sit down and chat with you."

Sam sighed in frustration. "Fine. Will you bail me out if I need help?"

Jess shrugged. "Only if I'm not laughing too hard."

Dean chuckled. "Go on, Dean Forrester, you'll be fine."

Shaking his head, Sam walked to the bench and sat down. He took out Jess's book and began reading, hoping that nobody would speak to him. A few minutes passed by and finally somebody sat down next to him. Sam kept reading, praying that whoever it was would see he was busy and leave.

"Interesting book you've got there. Where'd you get it from?" A male voice asked.

Sam put on a fake smile and glanced up at the man. He looked to be in his thirties, with short brown hair, hazel blue eyes, and an oval shaped face.

"Uh, the bookstore," Sam answered. "Why? You looking to buy a copy for yourself?"

The man nodded. "Well if I knew what it was about, I would. If it's something pornographic I can't bring it home because my mother would have a cow if she saw it laying around. Then again, maybe she'd read it. I've seen her read stuff like that before. Well I've seen it around the house."

Sam kept up his smile, but his eyes opened wide as he thought, _Who the hell am I talking to? Why is he talking about his mother reading pornos? If there was ever a time to interrupt, Jess, now would be it._

But Jess and Dean were behind the bushes laughing.

"Maybe you should go bail his out," Dean whispered through laughs.

Jess shook his head. "It's just starting to get interesting. I think I'll wait a while."

The man looked back at Sam. "Have you ever seen your mother's porno books laying around the house?"

"No, I don't think so," Sam answered, feeling awkward.

The man nodded his head. "Good. Don't ever pick them up and read them. It gives you a whole new perspective of your mother."

Sam was pretty sure that this man was Kirk, the one Jess had described. "Well thanks for that advice, Kirk. I'll take it into consideration. Now, if you don't mind, could I get back to reading?"

"Oh yeah, yeah. Books are good for reading. And throwing. They hurt. A lot. My fifth grade class used to play a game called Dodge Book where they would throw books at me sometimes. Anyways, I should go." Kirk stood up. "Bye, Dean."

Sam waved. "See ya, Kirk."

As soon as Kirk was out of view, Sam slumped down into the bench and sighed in relief. His test was finally over. "I hate you both, I hope you know that!" he called out to Dean and Jess.

"Who do you hate?" a female voice asked.

Sam looked up at the newcomer. She was a pretty girl, young looking with bright blue eyes, silky straight milk-chocolate brown hair, a friendly smile, and a school uniform and backpack. Sam wondered who this girl was.

He laughed nervously as he sat up straight. "Um, the characters in the book I'm reading," he answered, holding up the book.

The girl smiled, nodding her head. She looked closely at the book. "Oh, I think that's the same book Jess has been reading," she said, staring at the cover.

"Well now I might just have to burn it," Sam joked, remembering how Jess had said that this Dean Forrester guy hated him.

The girl shook her head. "Sorry, I shouldn't have brought it up."

"Oh, no, you're fine." Sam hoped he hadn't hurt her feelings or pissed off Jess. Sam was pretty sure that this must have been Rory.

"So, you're into those kind of mystery books now?"

Sam nodded, playing along. "Yeah, I just grabbed a copy from the bookstore, thought I'd try something new."

"I'm glad to see that you're reading something new. So how's school going? Are you keeping up in all your classes?"

Sam nodded. "Yup! You know me, hitting the books after hockey practice."

She looked at him funny for a second, as if she wondered what was up with him.

"So how's school going for you?" Sam asked, changing the subject.

"Good. I got an A on my essay for English, and we have another one coming up later in the week. Speaking of school," she glanced down at her watch, "I should get going. Say hi to Clara for me. Bye Dean."

"Bye Rory," Sam said, waving to her.

Rory waved back and walked away.

Before anyone else could approach him, Sam stood up and walked to the bushes, where Dean and Jess were. Sam whacked Jess on the head with his book and said, "Here you go. Happy I passed the tests?"

Jess glared at Sam for hitting him and shoved his book back in his pocket. He and Dean both stood up.

Dean chuckled, thinking of Kirk. "Man, I loved that dude talking about the pornos. I wish I could've seen your face, Sammy."

Sam gave Dean a bitch face. "I hope I never have to hear about him or mother ever again."

"Well after talking to Kirk and Rory, of all people, I think you're ready for Taylor. He's the town everything. Mayor, historian, whatever position of power there is, he's got it. But first, Dean, you can't come with us. Taylor will realize you're not from town and he'll ask too many questions."

"Where the hell am I supposed to go? Are there any motels here?"

Jess tilted his head in thought. "There's the Independence Inn. It's run by Lorelai, Rory's mom. You could book a room there."

Dean nodded. "Okay, well I guess I'll grab the Impala and head over there. Where's it at?"

Jess gave Dean the directions and he left the boys alone. Jess turned to Sam and said, "Let's do this, Dean."


	5. Chapter 5: The School-Ditching Twin

**A/N: Sorry the updates have been slow; I've been crazy busy! I'll try to update this as much as I can, but I'm going to be extremely busy the next few weeks. My goal is to write as much as possible, so be expecting updates about every day from today (Monday) until Thursday. I apologize that this chapter might be slow; it's a bit lighter. But I can give y'all a few spoilers for what's coming up. So, if you don't like spoilers, just remember I am thankful for your read and you proceed to the story. If you like spoilers than here you go: In the next few chapters, Sam and Dean will have a run-in with Lorelai, and finally they'll get to fight the monster, but who knows what kind of tricks this thing has up its sleeve, perhaps it will crawl inside the minds of the hunters? Maybe Sam will meet Dean F. And maybe Jess will be caught hunting by someone from Stars Hollow. You will all just have to wait and see! So, thanks for sticking with me! I love you guys!3 - LivingTheSPNLife**

**_ Dean W's POV_**

Once Jess had given him directions to the Independence Inn, Dean said his goodbyes to Sam and Jess and took off towards his car. He'd forgotten that he'd left it outside the dance studio, and he hoped that nobody was around to ask questions. Sam had also given Dean his laptop to put back in the Impala, so Dean was lugging that around as well.

Dean casually walked over to the Impala and was about to get inside when he heard a voice say, "Hello, sir, you're new around here."

Dean looked up to see a plump older woman, around her late 40s, with flame-red curly hair that surrounded her face and a cigarette in hand. She wore a flamboyant red and orange dress, begging for people to notice it. Dean smiled at the lady, trying to be as charming as possible so he could leave quicker.

"Hi. Yeah, I stopped by to visit some friends," Dean lied, keeping up his smile.

The woman checked him out from head to toe. "I hope you saved a visit for me, handsome." She took a drag of her cigarette.

Dean chuckled. "Why else would my car be here?"

The woman laughed and stuck out a hand. "I'm Patricia, but everyone around here calls me Miss Patty."

Dean took her hand and shook it. "I'm Dea... con. Deacon Smith." Dean figured that Sammy should be the only brother being called Dean in this town; otherwise things would get confusing for them both.

"Miss Patty, Justin keeps pulling my leaves!" a little girl cried from the door of the studio. She was dressed as a tree.

Patty turned to Dean. "I should really get back, but I hope to see you around Deacon. If you're in town long enough, you should check out the musical these kids will be in."

Dean nodded. "Maybe."

Dean opened the door to the Impala and slid inside, setting Sam's laptop on the passenger seat. He turned on the engine and was about to pull away when he saw Patty and the kid waving at him. Dean smiled and waved back and pulled onto the main road. The drive to the inn wasn't long, and soon he found himself parked in front of a grand structure. Dean got out of the car and walked inside the busy inn and to the front desk.

A dark-skinned gentleman dressed in a suit with a nametag reading Michele stood behind the desk doing some paperwork. Dean walked up to him and waited for the man to notice him, but he never did, not until Dean cleared his throat did the man look up.

"Welcome to the Independence Inn," he said distastefully in a French accent, "How may I help you?"

"I would like a room with two beds, please," Dean said, taking out his wallet.

"Two beds all to yourself, how wonderful. How many nights?"

Dean glanced at the Michele's comment. "I'm staying here with a friend. I don't know how long we're staying, but I can give you my credit card number so you can charge us once we check out." Dean handed him the card.

Michele grabbed the credit card and began to type in the number to their computer's database. Michele handed it back to him and fetched Dean two keycards. "Two keycards for you and your 'friend'. Enjoy your stay." Michele flashed Dean a fake smile.

Dean took the keys. "Thanks Michelle!" Dean called out as he headed toward the door.

"It's Michele! Like Me-shell!" Michele called back, making Dean smirk. Oh how he loved pissing people off.

**_ Sam and Jess's POV_**

"Taylor Doosey will be right inside there," Jess said, pointing to a yellow building on the street corner. In big letters, the building read 'Doosey's Market'. "Do you remember what I told you he looked like?"

Sam nodded. "Annoying guy with white, balding hair. I got it. Wish me luck."

Sam took in a deep breath and began walking toward the market. He hoped he would be able to pull this off. Sure, he and Dean had plenty of experience impersonating all kinds of people – marshals, wildlife officials, homeland security, college students; the list was endless – but impersonating a person that people around here knew personally was another story. There was so much to remember from the way they behaved to their background information.

And that was when Sam realized something.

He turned around and began walking toward Jess.

"What's up? Why aren't you going in?" Jess asked when Sam was closer.

"Today is Monday, right?"

Jess nodded. "Yeah, so? What's your point?"

"Okay, so problem. This Dean guy is seventeen. He goes to school. It's a school day, Jess. I can't walk in there or I'll get questions as to why I'm not in school."

"Just make up some bullshit excuse."

"And what happens when the real Dean hears about this and wants to look for his mysterious, school-ditching twin?"

Jess laughed. "School-ditching twin? Good one."

"I'm serious, Jess! And shouldn't you be I school?"

Jess shrugged. "Don't feel like it. Besides, don't you think we have bigger issues at hand than whether I go to school or not?"

Sam shook his head. "Just go, Jess. It might not be fun, but the education is worth it."

Jess didn't say anything.

"Jess, we can't do anything else until Dean gets out of school. So just go. It's not like you have anything better to do, right?"

Jess sighed. "Then what are you going to do?"

"Head back to the Independence Inn with Dean. Take nap or something. Need a ride to the school?"

Jess shook his head. "No, I can take my car. It's back near Patty's, but I can get it."

"Okay, well we'll see you after school," Sam said, taking out his phone to call Dean.

After Jess had finished school, he met Sam and Dean at the gazebo in the middle of town. Sam had on a hoodie so nobody would see him and mistake him for Dean Forrester. He'd had too many of those encounters already.

Since Sam already had a good idea of who Taylor was, he walked over to Doosey's Market before Jess arrived. He walked up to the door with its green sign saying that apples were on sale and opened it. A gush of cool air and the aroma of apples, oranges, and all kinds of fruits. A little bell rang as soon as he walked inside, but that barely registered in his mind.

Right now, it felt as though Sam was looking into a mirror. At the register stood Dean Forrester. He looked exactly like Sam aside from the goofy haircut, the too-big-for-me clothes, and the green apron he wore with Doosey's Market on it. Dean was busy scanning the price of a customer's item to notice Sam's presence, so Sam hightailed it out of there.

He sped-walked over to Dean and a newly arrived Jess.

"Thanks for telling me that Dean works at the market," Sam barked at Jess, pulling up his hoodie.

Jess shrugged. "So I forgot to throw in that detail. Big deal."

"Do you know when he gets off work?"

"Nope."

"Well that's helpful. So, what now guys?"

"We should just wait until nightfall. That's the only time we'll actually be able to do something. It beats just standing around here to think of some lame-ass plan," Dean said.

Sam and Jess nodded. "Sounds good. I have work in an hour anyways," Jess said. "So when do you guys want to meet up at? Midnight?"

"Where do you work?" Sam asked.

Jess hesitated a moment. "Wal-Mart."

Dean chuckled. "You work at Wal-Mart? That's too good. A hunter helping customers at Wal-Mart. That's what your life's movie will be about."

"Laugh it up all you want, but at least I get paid. Now, are we meeting up at midnight? We can meet up here at the gazebo."

"Yeah, that sounds good," Sam said.

Jess nodded, said, "See you later, Deacon and the school-ditching twin," and headed for his car, jetting off to work, leaving Dean to turn to Sam in confusion.

"School-ditching twin?" he asked.

"Yeah, well I told you what happened this morning. And I kind of called myself that."

Dean burst into laughter. "Okay, school-ditching twin, let's head back to the inn," Dean said, walking towards the Impala. He could not stop laughing.

"Shut up," Sam said, following his brother's lead. He hoped that nickname wouldn't stick.


	6. Chapter 6: It's A Date!

**A/N: Hey guys! Told you I would make updates every day! I know this chapter is shorter than the previous ones, but it's a chapter, right? Well, I hope you all enjoy it! Sorry there's no Jess in here for those of you that like him; I promise that he will be in the next chapter! Anyways, thanks for sticking with me! I love you all! Peace out girl scouts!3  
-LivingTheSPNLife  
_  
Sam and Dean_ W's_ POV_**

"So what's the plan for the next few hours?" Sam asked as he and Dean walked through the doors to the inn. "I don't want to just sit in the room until it's time to go."

"Well you can't go anywhere in the town or you'll be mistaken as -"

"Dean! What are you doing here?" a woman called out from across the room.

_Damn it,_ Sam thought as he looked up to see the woman. She was beautiful. She looked to be in her early thirties with dark chocolate brown hair that fell a few inches below her shoulder in cascading waves, a large grin, and a white, button up shirt and a black shirt polished off with a pair of black, knee-high boots. She looked a lot like the Rory girl he had met earlier. Wait, hadn't Jess mentioned that Rory's mother worked at an inn? Her name was…

"Lorelai, hey," Sam greeted, returning her friendly smile. "How have you been?"

"I've been doing good. What about you, Dean?" she asked, walking over.

"I've been pretty good myself, thanks."

"Have you done something different with your hair?"

_Shit. Dean doesn't have my haircut._ "Uh, yeah. I'm changing it up. Trying new things, you know. You only live once, why not try different haircuts along the way."

"I like it. Anyways, what are you doing here?" Lorelai asked once she reached the brothers. She sounded curious, not rude.

"I'm here with my cousin," Sam said, going with the first thing that popped inside of his head. He gestured to Dean.

Dean smiled and offered his hand. Lorelai took it and shook it. "Hi, I'm Deacon. I've never been here before so, uh, Dean here offered to show me around. Said this was the best place to stay."

"Well, welcome to Stars Hollow, Deacon. I'm sure you're going to like it. So are you just visiting for a few days?"

Dean nodded. "Yeah, I was just working a construction job down in Hartford and figured I'd stop by and see where my aunt and uncle moved to."

"I bet that's where Dean gets his handyman skills. Are you guys hungry?"

Dean looked at Sam and nodded. "Yeah, I could go for some food," Dean said, his stomach grumbling.

Lorelai grinned. "Perfect. Well, as Dean knows, at the Independence Inn we offer breakfast, lunch, and dinner. Breakfast is free, but just for you two, dinner will be on the house. We have our wonderful chef Sookie St. James who cooks all of our meals."

"Sounds great," Dean said.

"I'll show you to the dining hall, then," Lorelai said, leading them through the inn.

"She's a babe," Dean muttered to Sam as they followed her.

"We're here for a job Dean," Sam said with a roll of his eyes. The last thing they needed was for Dean to hook up with Jess's girlfriend's mom. Talk about awkward.

"Here, you guys can sit at this table." Lorelai brought them to a small table with a white cloth on it and small a vase of flowers for the centerpiece with menus standing next to it.

Sam and Dean sat down and Lorelai handed them the menus. "Take your time deciding what you want. Just call me over when you're ready."

"Thanks, Lorelai," Sam said as she left to check something up at the front desk. He looked down at his menu and began looking through its contents.

"Seriously, how do you _not_ think she's hot?" Dean said, looking at Sam over the top of his menu.

Sam rolled his eyes. "I never said that. Yeah, she's beautiful, but do you really expect her to take one look at you and decide that she wants to have sex with you, some stranger she's never met before?"

Dean shrugged. "Some girls do."

"Well, it's your life. You ready to order?"

Dean nodded and called over for Lorelai. "What can I get you boys?" she asked.

"Water and the chef's salad for me," Sam said, handing Lorelai his menu.

Dean smiled flirtatiously and said, "I'll take a Coke and the bacon burger. And could we have some apple pie for dessert?"

Lorelai returned his smiled. "Coming right up."

A few minutes passed and Lorelai came back with their drinks. "You're food will be ready in a little bit."

Before she turned to leave, Dean stopped her. "Lorelai, I know this might seem random, but do you have a boyfriend?"

Sam's eyes widened in shock and he kicked Deans leg under the table. Dean flinched at the pain for a second but regained his composure. He wasn't going to let Sam stop him from talking to Lorelai.

"No, I don't, actually," Lorelai answered.

"Well would you like to go out for coffee or something tomorrow?"

Lorelai smiled and nodded her head. "Yeah, I would like that. Just find me at the front desk sometime tomorrow and we'll go. I know a great spot that has awesome coffee."

"Sounds great," Dean said, taking a sip of his Coke.

"Dean!" Sam said in a hushed whisper.

Dean shrugged. "What? It's an innocent little date. You need to learn how to have fun, Sammy. There's no harm done. We'll finish up the job tonight and then I'll go on the date and we can leave."

Sam sighed. "Fine."


End file.
